Nitrogen → 2-Amino-5-(4-nitrophenyl)furan-3,4-dicarboxylic acid diethylester

反応式

[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)Cl)[CH3:2].[CH2:19]([O:21][C:22](=[O:26])[CH2:23][C:24]#[N:25])[CH3:20].[Na].N#N>C1COCC1>[CH2:19]([O:21][C:22]([C:23]1[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:18])=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[O:17][C:24]=1[NH2:25])=[O:26])[CH3:20]

参加物

実験手順

105 g (0.39 mols, 1 eq) of 4-nitrobenzoyl-chloroacetic acid ethyl ester are dissolved in 600 ml of THF. To this solution are added, on a water bath (T=35° C.), in portions, 49.4 g (0.37 mols) of finely ground sodium cyanoacetic acid ethyl ester (preparation: Chem, Ber. 1962, 95, 307-318.). It is stirred over night (under N2), fully concentrated by evaporation, and extracted with H2O and CH2Cl2. The combined CH2Cl2 phase is washed with H2O, and finally dried over MgSO4 and freed from solvent. Crystallisation from toluene yields the title compound, m.p.: 174-177° C.